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Coolio boy

Coolio boy is you but cool!
Person 1:hey I am such a Coolio boy

Person2:hey me too!!
person1shut the fuck up
by therealcoolioboy June 15, 2024
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coolio joe bob

Person 1: I called an uber.
Person 2: coolio joe bob.
by lisabella June 29, 2016
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Steve Coolio

The greatest R&B singer since Chris Brown in 2005. Often proclaimed by some to be better than Chris Brown.
Hey man, have you heard the new Steve Coolio song? That shit hits harder than Chris Brown
by JayDaWalker2005 September 27, 2022
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coolio

you are so coolio
by smypad October 16, 2018
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Coolioness

“Bro you have so much coolioness today
Thanks bro!!!”
by snellie January 1, 2023
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Caleb the coolio

caleb is an awesome guy you can always count on, hes funny, great awesome, someone you would wish to be friends with. He has an awesome friend group mostly known as the coolios, he likes writing, not that smart(im sorry), but is still awesomly cool. Hes an artsy guy, very great at drawing ( very cool )! Hes one of my greatest friends of the greatest greats! ( makes total sense but yk )..
Caleb the coolio is such a god damn nerd but is so cool?!?!
by a stupid ass loser June 6, 2022
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Coolio

Person has made/done/looks like something that is very cool and a lot of people like them.
Sarah : Hey Lily, I made a YouTube channel and i have 10,000 subscribers olny in 2 weeks!
Lily Repsonds : Woah, Sarah. You are very coolio!
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